4-Amino-3-[(4-methoxy-phen-yl)amino-meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The mol-ecule of the title compound, C(10)H(13)N(5)OS, is approximately planar, the dihedral angle between the triazole and benzene rings being 4.53 (10)°. The amino group adopts a pyramidal configuration. In the crystal structure, mol-ecules are linked into two-dimensional networks parallel to (001) by inter-molecular N-H⋯S and N-H⋯N hydrogen bonds. In addition, an S⋯S short contact of 3.3435 (7) Å is observed.

Related literature

For the pharmacological applications of 1,2,4-triazole derivatives, see: Amir et al. (2008 ▶); Isloor et al. (2009 ▶); Krzysztof et al. (2008 ▶); Kuş et al. (2008 ▶); Padmavathi et al. (2008 ▶). For the preparation, see: Holla & Udupa (1992 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H13N5OS

M = 251.31

Monoclinic,

a = 11.5142 (2) Å

b = 5.8804 (1) Å

c = 16.6891 (3) Å

β = 95.292 (1)°

V = 1125.17 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.33 × 0.18 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.913, T max = 0.994

5827 measured reflections

2365 independent reflections

2126 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.068

S = 1.04

2365 reflections

171 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 588 Friedel pairs

Flack parameter: 0.03 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032607/ci2889sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032607/ci2889Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H13N5OS	F(000) = 528
Mr = 251.31	Dx = 1.484 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2961 reflections
a = 11.5142 (2) Å	θ = 3.6–32.2°
b = 5.8804 (1) Å	µ = 0.28 mm−1
c = 16.6891 (3) Å	T = 100 K
β = 95.292 (1)°	Plate, colourless
V = 1125.17 (3) Å3	0.33 × 0.18 × 0.02 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	2126 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
Tmin = 0.913, Tmax = 0.994	k = −8→5
5827 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0277P)2 + 0.6764P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2365 reflections	Δρmax = 0.33 e Å−3
171 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 588 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (7)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.37035 (4)	0.34412 (9)	0.03759 (3)	0.01571 (11)
O1	−0.26796 (11)	1.2919 (3)	0.42305 (8)	0.0248 (4)
N1	0.07536 (13)	0.3929 (3)	0.13658 (9)	0.0171 (4)
N2	0.15394 (14)	0.2872 (3)	0.09067 (10)	0.0164 (4)
N3	0.23563 (13)	0.5947 (3)	0.13167 (9)	0.0136 (3)
N4	−0.02128 (14)	0.6826 (3)	0.24608 (10)	0.0167 (4)
N5	0.30984 (14)	0.7845 (3)	0.14247 (10)	0.0171 (4)
C1	0.25184 (15)	0.4074 (3)	0.08580 (11)	0.0144 (4)
C2	0.12844 (15)	0.5803 (4)	0.16083 (11)	0.0138 (4)
C3	0.08129 (16)	0.7617 (4)	0.21027 (12)	0.0158 (4)
H3A	0.1404	0.8072	0.2524	0.019*
H3B	0.0613	0.8933	0.1768	0.019*
C4	−0.08548 (14)	0.8413 (4)	0.28707 (10)	0.0146 (3)
C5	−0.04122 (16)	1.0556 (4)	0.31036 (12)	0.0174 (4)
H5A	0.0307	1.1019	0.2950	0.021*
C6	−0.10392 (16)	1.1985 (4)	0.35610 (12)	0.0187 (4)
H6A	−0.0732	1.3398	0.3715	0.022*
C7	−0.21184 (16)	1.1350 (4)	0.37941 (11)	0.0168 (4)
C8	−0.25711 (16)	0.9225 (4)	0.35578 (11)	0.0174 (4)
H8A	−0.3295	0.8776	0.3708	0.021*
C9	−0.19487 (15)	0.7792 (4)	0.31039 (11)	0.0163 (4)
H9A	−0.2261	0.6384	0.2949	0.020*
C10	−0.37125 (17)	1.2205 (4)	0.45705 (12)	0.0219 (5)
H10A	−0.3982	1.3406	0.4896	0.033*
H10B	−0.3545	1.0881	0.4897	0.033*
H10C	−0.4305	1.1848	0.4147	0.033*
H1N2	0.1335 (18)	0.175 (4)	0.0617 (13)	0.016 (6)*
H1N4	−0.063 (2)	0.601 (5)	0.2156 (15)	0.032 (7)*
H1N5	0.381 (2)	0.728 (5)	0.1550 (16)	0.047 (8)*
H2N5	0.3141 (19)	0.845 (6)	0.0921 (15)	0.042 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.01344 (18)	0.0157 (2)	0.0184 (2)	0.0019 (2)	0.00344 (15)	−0.0002 (2)
O1	0.0220 (7)	0.0201 (9)	0.0342 (8)	−0.0015 (6)	0.0123 (6)	−0.0096 (7)
N1	0.0157 (7)	0.0161 (10)	0.0201 (8)	−0.0007 (7)	0.0052 (6)	0.0000 (7)
N2	0.0186 (7)	0.0117 (9)	0.0197 (8)	−0.0021 (6)	0.0050 (6)	−0.0030 (7)
N3	0.0126 (7)	0.0149 (9)	0.0135 (7)	−0.0008 (6)	0.0015 (6)	−0.0003 (7)
N4	0.0150 (8)	0.0149 (9)	0.0208 (9)	−0.0039 (7)	0.0051 (7)	−0.0033 (7)
N5	0.0142 (7)	0.0148 (9)	0.0220 (9)	−0.0050 (6)	0.0006 (6)	−0.0019 (7)
C1	0.0143 (8)	0.0155 (10)	0.0135 (8)	0.0025 (7)	0.0011 (7)	0.0001 (7)
C2	0.0132 (8)	0.0156 (10)	0.0126 (9)	0.0022 (7)	0.0015 (7)	0.0029 (8)
C3	0.0151 (8)	0.0140 (10)	0.0183 (9)	−0.0012 (7)	0.0020 (7)	0.0006 (8)
C4	0.0153 (7)	0.0154 (9)	0.0132 (7)	0.0032 (9)	0.0012 (6)	0.0006 (10)
C5	0.0139 (9)	0.0176 (11)	0.0211 (10)	−0.0015 (8)	0.0043 (7)	0.0005 (8)
C6	0.0188 (9)	0.0146 (10)	0.0228 (10)	−0.0027 (8)	0.0020 (8)	−0.0037 (8)
C7	0.0174 (9)	0.0165 (10)	0.0167 (9)	0.0015 (8)	0.0030 (7)	−0.0005 (8)
C8	0.0157 (9)	0.0184 (10)	0.0187 (9)	−0.0014 (8)	0.0044 (7)	0.0013 (8)
C9	0.0163 (8)	0.0121 (10)	0.0203 (9)	−0.0024 (7)	0.0002 (7)	−0.0006 (8)
C10	0.0177 (9)	0.0258 (13)	0.0228 (10)	0.0016 (9)	0.0057 (8)	−0.0032 (9)

S1—C1	1.6883 (18)	C3—H3A	0.97
O1—C7	1.373 (2)	C3—H3B	0.97
O1—C10	1.427 (2)	C4—C5	1.401 (3)
N1—C2	1.306 (3)	C4—C9	1.401 (2)
N1—N2	1.386 (2)	C5—C6	1.383 (3)
N2—C1	1.339 (2)	C5—H5A	0.93
N2—H1N2	0.84 (2)	C6—C7	1.387 (3)
N3—C1	1.364 (3)	C6—H6A	0.93
N3—C2	1.370 (2)	C7—C8	1.397 (3)
N3—N5	1.407 (2)	C8—C9	1.377 (3)
N4—C4	1.407 (3)	C8—H8A	0.93
N4—C3	1.448 (2)	C9—H9A	0.93
N4—H1N4	0.82 (3)	C10—H10A	0.96
N5—H1N5	0.89 (3)	C10—H10B	0.96
N5—H2N5	0.92 (3)	C10—H10C	0.96
C2—C3	1.482 (3)
C7—O1—C10	117.60 (17)	H3A—C3—H3B	108.1
C2—N1—N2	103.83 (15)	C5—C4—C9	118.09 (18)
C1—N2—N1	113.14 (16)	C5—C4—N4	122.53 (16)
C1—N2—H1N2	125.0 (14)	C9—C4—N4	119.3 (2)
N1—N2—H1N2	120.6 (14)	C6—C5—C4	120.33 (17)
C1—N3—C2	108.88 (16)	C6—C5—H5A	119.8
C1—N3—N5	126.84 (15)	C4—C5—H5A	119.8
C2—N3—N5	124.04 (17)	C5—C6—C7	121.20 (19)
C4—N4—C3	118.22 (18)	C5—C6—H6A	119.4
C4—N4—H1N4	112.7 (18)	C7—C6—H6A	119.4
C3—N4—H1N4	112.5 (17)	O1—C7—C6	116.46 (18)
N3—N5—H1N5	105.8 (19)	O1—C7—C8	124.69 (17)
N3—N5—H2N5	105.9 (18)	C6—C7—C8	118.83 (18)
H1N5—N5—H2N5	103 (2)	C9—C8—C7	120.19 (17)
N2—C1—N3	103.45 (15)	C9—C8—H8A	119.9
N2—C1—S1	129.38 (15)	C7—C8—H8A	119.9
N3—C1—S1	127.15 (15)	C8—C9—C4	121.4 (2)
N1—C2—N3	110.68 (18)	C8—C9—H9A	119.3
N1—C2—C3	126.50 (17)	C4—C9—H9A	119.3
N3—C2—C3	122.78 (18)	O1—C10—H10A	109.5
N4—C3—C2	110.69 (17)	O1—C10—H10B	109.5
N4—C3—H3A	109.5	H10A—C10—H10B	109.5
C2—C3—H3A	109.5	O1—C10—H10C	109.5
N4—C3—H3B	109.5	H10A—C10—H10C	109.5
C2—C3—H3B	109.5	H10B—C10—H10C	109.5
C2—N1—N2—C1	−0.9 (2)	N3—C2—C3—N4	−168.35 (17)
N1—N2—C1—N3	1.1 (2)	C3—N4—C4—C5	−14.9 (3)
N1—N2—C1—S1	179.40 (14)	C3—N4—C4—C9	169.36 (17)
C2—N3—C1—N2	−0.9 (2)	C9—C4—C5—C6	1.0 (3)
N5—N3—C1—N2	−175.43 (17)	N4—C4—C5—C6	−174.84 (19)
C2—N3—C1—S1	−179.25 (15)	C4—C5—C6—C7	−0.5 (3)
N5—N3—C1—S1	6.3 (3)	C10—O1—C7—C6	−171.73 (18)
N2—N1—C2—N3	0.2 (2)	C10—O1—C7—C8	10.0 (3)
N2—N1—C2—C3	177.94 (18)	C5—C6—C7—O1	−178.46 (18)
C1—N3—C2—N1	0.4 (2)	C5—C6—C7—C8	−0.1 (3)
N5—N3—C2—N1	175.13 (17)	O1—C7—C8—C9	178.47 (18)
C1—N3—C2—C3	−177.35 (17)	C6—C7—C8—C9	0.2 (3)
N5—N3—C2—C3	−2.7 (3)	C7—C8—C9—C4	0.2 (3)
C4—N4—C3—C2	−172.48 (15)	C5—C4—C9—C8	−0.8 (3)
N1—C2—C3—N4	14.2 (3)	N4—C4—C9—C8	175.13 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.84 (2)	2.55 (2)	3.3672 (18)	164 (2)
N4—H1N4···N5ii	0.82 (3)	2.60 (3)	3.410 (2)	169 (3)
N5—H1N5···N1iii	0.89 (2)	2.48 (2)	3.133 (2)	130 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.84 (2)	2.55 (2)	3.3672 (18)	164 (2)
N4—H1N4⋯N5ii	0.82 (3)	2.60 (3)	3.410 (2)	169 (3)
N5—H1N5⋯N1iii	0.89 (2)	2.48 (2)	3.133 (2)	130 (2)

Symmetry codes: (i) ; (ii) ; (iii) .